Supplementary Material. Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction
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1 Supplementary Material Photostimulated synthesis of 2-(diphenylphosphino)benzoic acid by the S RN 1 reaction Silvia M. Barolo, Sandra E. Martín,* Roberto A. Rossi* INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba, 5000, Argentina rossi@fcq.unc.edu.ar Table of Contents Results and Discussion of Annex Material S2 Experimental Section S3 General S3 Materials S3 Representative Procedure for Photostimulated Reactions in Liquid Ammonia S3 1 H NMR spectrum of Ethyl 2-(diphenylphosphoryl)benzoate (4) S5-S7 13 C NMR spectrum of Ethyl 2-(diphenylphosphoryl)benzoate (4) S8-S9 31 P NMR spectrum of Ethyl 2-(diphenylphosphoryl)benzoate (4) S10 1 H-NMRspectrum of Ethyl benzoate (5) S11-S12 13 C-NMR spectrum of Ethyl benzoate (5) S13-S14 1 H-NMR spectrum of Ethyl 2-chlorobenzoate (6) S15-S16 13 C-NMR spectrum of Ethyl 2-chlorobenzoate (6) S17-S18 MS of Ethyl benzoate (5) and Ethyl 2-chlorobenzoate (6) S19 Page S1
2 Results and Discussion of Annex Material To extend the studies, we conducted news experiments in liquid ammonia at -78 ºC with 1 equiv. of 1, 1 equiv. of Ph 2 P ions and 2.5 h of stirring before adding 2-chlorobenzoate ion (1), as those previously reported. 1 However, the reactions were carried out in a photochemical reactor equipped with two metal iodide lamps of 400 W (Philips, Model HPI-T, water refrigerated), and quenched by adding NH 4 NO 3 in excess instead of adding THF at 30 min of reaction. Typically, product analyses were conducted by esterification of the phosphine to the corresponding esters (ethyl 2-(diphenylphosphoryl)benzoate (4), ethyl benzoate (5) and ethyl 2-chlorobenzoate (6)) with ensuing determination by GC. Results are summarized in Table S1. When the photostimulated reaction of 1 with Ph 2 P ions was carried out in this condition, the substitution product was obtained only in 11% yield and 75% of the substrate remained unaltered (entry 1, Table S1). The reaction did not occur in the dark (entry 2, Table S1). In addition, the photostimulated reactions were also inhibited by small amounts of electron acceptors (m-dnb) or free-radical traps (TEMPO) (entries 3 and 4, Table S1). Once again, all these results suggets that the reaction proceeds through the S RN 1 mechanism. In adition, we shows that without quenched by adding NH 4 NO 3 in excess, the reaction continue to progress beyond the addition of THF, during the time of solvent evaporation and consequente increase in temperature (-78 to -33 ºC) (compare entry 1, Table 2 with entry 1, Table S1). Table S1. Reactions of 1 with Ph 2 P ions under the experimental conditions reported in ref. 1 and quenched with NH 4 NO 3 Entry Conditions a Cl - (%) b 4 (%) c 6 (%) c 5 (%) c 1 NH 3, -78ºC, hv, 30 min >5 2 d NH 3, -78ºC, dark, 30 min >1 -- ca e NH 3, -78ºC, hv, 30 min >1 -- ca f NH 3, -78ºC, hv, 30 min >1 -- ca a Reactions carried out under N 2 in ml of ammonia at -78ºC, with 1 equiv. (4.44 mmoles) of 1, 1 equiv. (4.44 mmoles) of Ph 2 P ions and 2.5 h of stirring before adding 1 and 0.5 h of stirring before adding of an excess of NH 4 NO 3. Is important to note that t-buoh was not added. Irradiation was conducted in a photochemical reactor equipped with two 400 W lamps refrigerated with air and water unless otherwise indicated. b Determined potentiometrically. c Yields were determined by GC (internal standard method). d 2-Chlorobenzoic acid was added in one portion. e 20 mol % of m-dnb was added. f 20 mol % of TEMPO was added. Page S2
3 Experimental Section General. Gas chromatographic analyses were performed on a Hewlett Packard 5890 series II with a flame ionization detector and equipped with the following column: HP1 column (0.53 mm x 5m). Quantification by GC was performed by the internal standard method. Gas Chromatographic-Mass Spectrometer analyses were carried out on a Shimadzu QP-5050 spectrometer equipped with a quadrupole detector and a VF-5 ms column (30 m x 0.25 mm x 0.25 μm). 1 H NMR ( MHz), 31 P NMR (162 MHz) and 13 C NMR ( MHz) spectra were recorded on a High Resolution Spectrometer Bruker Advance 400 in CDCl 3 as solvent and against internal TMS ( 1 H) and external 85% phosphoric acid ( 31 P). Coupling constants (J) are given in Hz units. Irradiation was conducted in a reactor equipped with two 400-W lamps of metal iodide (Philips, Model HPI-T) refrigerated with water. An Orion 420A phmeter with Ag/Ag + electrode was used for the potentiometric titration of halide ions in the aqueous phases. Materials C 6 H 5 CO 2 H, 2-ClC 6 H 4 CO 2 H, Na metal, Ph 3 P, t-buoh, NH 4 NO 3, EtOH and H 2 SO 4 were commercially available and used as received from the supplier. THF was dried over Na metal and benzophenone, and distilled under atmosphere of N 2. All solvents were analytical grade and used as received from the supplier. Silica gel ( mm Macherey-Nagel) was used in column chromatography. Ethyl benzoate and ethyl 2- chlorobenzoate were prepared according to the literature procedure. 2 Representative Procedure for Photostimulated Reactions of 1 with Ph 2 P ions in Liquid Ammonia Liquid ammonia (150 ml), previously dried with Na metal under N 2, was condensed into a 250 ml three-necked, round-bottomed flask equipped with a coldfinger condenser charged with ethanol, a nitrogen inlet, and a magnetic stirrer. PPh 3 ( g, 0.55 mmol) was then added, and Na metal was introduced in small pieces; addition was continued until the solution kept its dark brown color for at least 15 min. After its color turned red, t-buoh (0.5 ml, 0.55 mmol) was added to eliminate the H 2 N anions formed. An orange solution of Ph 2 P ions was obtained. 2- Chlorobenzoic acid was added to the solution to form 1 ( g, 0.5 mmol), and the mixture was irradiated for 120 min with two metal iodide lamps of 400 W (Philips, Model HPI-T, water refrigerated). The reaction was quenched with an excess of NH 4 NO 3 and the liquid ammonia was allowed to evaporate. Water (50 ml) was added to the residue and HCl was afterwards added until the aqueous phase reached ph 1-2. The Page S3
4 aqueous phase was extrated with ethyl acetate (3 x 30 ml) and the combined organic layers were washed with H 2 O (20 ml) and dried over anhydrous MgSO 4; the solvent was evaporated under vacuum. The chloride ions in the aqueous solution were determined by potentiometry. The crude products were mixed with EtOH (1.8 ml, 30.8 mmol) and concentrate H 2 SO 4 (0.05 ml, 0.94 mmol) in a 10 ml tube sealed and equipped with a magnetic stirrer. The mixture was heated to 80 C for 4 days. The excess of EtOH was eliminated on a rotary evaporator and allowed cooling. The residue was dissolved with water (50 ml) and NaHCO 3 was then added until have ph 8-9. The aqueous phase was extracted with ethyl acetate (3 x 30 ml) and the combined organic layers were washed with H 2 O (20 ml), dried over anhydrous MgSO 4 and then quantified by GC using the internal standard method. Alternatively, in other runs the solvent was removed under reduced pressure and the product ethyl 2-(diphenylphosphoryl)benzoate (4) 3 was purified by column chromatography on silica gel eluting with a dichloromethane / etanol gradient (100:0 95:5) as a colourless liquid. 1 H NMR ( MHz, CDCl 3 ): H (1H aro, m, 1CH), (13 H aro, m, 13CH), 3.97 (2H, q, J HH = 7.2 Hz, CH 2 CH 3 ), 1.00 (3H, t, J HH = 7.2 Hz, CH 2 CH 3 ). 13 C NMR ( MHz, CDCl 3 ): C (d, J = 3 Hz), (d, J = 6 Hz), (d, J = 10 Hz), (d, J = 108 Hz), (d, J = 99 Hz), (d, J = 10 Hz), (d, J = 3 Hz), (d, J = 12 Hz), (d, J = 8 Hz), (d, J = 13 Hz), (s, CH 2 CH 3 ), (s, CH 2 CH 3 ). 31 P NMR (162 MHz, CDCl 3 ): P MS, m/z (%) = 350 (M +, 2), 349 (4), 322 (30), 321 (88), 305 (21), 303 (25), 278 (11), 277 (35), 274 (20), 273 (100), 257 (16), 246 (17), 245 (87), 229 (25), 228 (13), 227 (31), 201 (15), 200 (16), 199 (35), 183 (12), 168 (11), 167 (22), 153 (17), 152 (51), 105 (12), 77 (56), 51(20). ESI-HRMS Anal. Calcd for C 21 H 19 O 3 PNa + (M+ Na + ) , found References 1. Kemme, S. T.; Schmidt, Y.; Grünanger, C. U.; Laungani, A. C.; Herber, C.; Breit, B. Synthesis 2010, Furniss, B. S.; Hannaford, A. J.; Smith P. W. G.; Tatchell, A. R. Vogel s Textbook of Practical Organic Chemistry, 5th Edn., Addison-Wesley, 1989, pp Crich, D.; Dyker, H. Tetrahedron Lett. 1989, 30, 475. Page S4
5 ppm Page S5
6 ppm Page S6
7 ppm ppm Page S7
8 ppm Page S8
9 ppm ppm Page S9
10 ppm Page S10
11 ppm Page S11
12 ppm Page S12
13 ppm Page S13
14 ppm Page S14
15 ppm Page S15
16 ppm Page S16
17 Page 100 S ppm ARKAT-USA, Inc
18 ppm Page S18
19 Ethyl benzoate (5). MS: m/z (%) = 151 (2); 150 (19); 122 (28); 106 (9); 105 (100); 84 (7); 78 (6); 77 (49); 76 (6); 51 (28); 50 (9); 49 (7). Ethyl 2-chlorobenzoate (6). MS: m/z (%) =185 (3); 184 (12); 158 (8); 156 (26); 141 (31); 140 (10); 139 (100); 113 (10); 111 (27); 76 (10); 75 (31); 74 (7); 51 (7); 50 (16); 49 (7). Page S19
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